A Travel Price Comparison for Families, Couples, and Backpackers Grand Cayman vs. Berkshires for Vacations, Tours, and Honeymoons

Should you visit Grand Cayman or Berkshires?

Which is cheaper to visit? Which is more expensive for vacation?

Which city should you visit? Read on to compare the activities as well as the prices of travel for Grand Cayman and Berkshires. We'll break down costs for accommodation, food, transportation and more to help you learn more about these two destinations. Then, you can figure out if either of these two places are accessible based on your travel budget, schedule, and interests. So, let's dig into it.

Where Should I go: Grand Cayman or Berkshires?

Grand Cayman

When people think of the Cayman Islands, they typically think of offshore bank accounts and sunny, cruise ship ports. Grand Cayman has more to offer travelers than a playground for the wealthy or a short stopover for cruise passengers. This tropical island is the largest of the three Cayman Islands, it is a shopper's heaven, a center for global finance and an ideal vacation spot.

Berkshires

The Berkshires are a popular highland destination in the western part of Massachusetts and northwest Connecticut. The region has scenic landscape, hiking, lakes, recreational opportunities and other outdoor experiences. The Berkshires also has an impressive cultural scene with music, arts, museums, and live theaters.

The Berkshires can be a bit expensive to visit if you stay at a luxury resort and take advantage of the award winning restaurants in the area. Alternatively, the experience can be equally rewarding by camping, picnicking, and spending your time hiking and enjoying the beautiful natural setting.

For some great organized tour ideas, see The Best Photography Tours in United States of America, and The Best Camping Tours in United States of America.


Which place is cheaper, Berkshires or Grand Cayman?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Grand Cayman is $214, while the average daily cost in Berkshires is $244. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Grand Cayman and Berkshires in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Grand Cayman $150
    Berkshires $141
  • Accommodation Typical double-occupancy room
    Grand Cayman $300
    Berkshires $282
Compare Hotels in Grand Cayman and Berkshires

Looking for a hotel in Grand Cayman or Berkshires? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Grand Cayman


Hotels in Berkshires


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Grand Cayman Hotel Prices and Berkshires Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Grand Cayman $31
    Berkshires $47

Hired Cars and Shuttles in Grand Cayman

Also for Grand Cayman, here are a few examples of actual transportation services:

  • Airport Transfer - Owen Roberts Intl Airport to GeorgeTown or Seven Mile Beach: $88
  • Airport Transfers to North Side Accommodation (GCM Grand Cayman): $265
  • George Town / 7- Mile Beach area to George Town Port -Departure Private Transfer: $53
  • George Town Cruise Port to George Town or 7-Mile Beach -Arrival Private Transfer: $53
  • George Town Port to George Town / 7-Mile Beach area -Round-Trip Private Transfer: $107
  • George Town Port to Owen Roberts Airport (GCM) - Departure Private Transfer: $53
  • Privat Transfer from Owen Roberts Airport GCM to George Town Port: $53
  • Private Transfer from George Town Port to George Town or 7-Mile: $53
  • Private Transfer from George Town Port to Owen Roberts AirportGCM: $53
  • Private Transfer from George Town or 7 Mile to George Town Port: $53

Is it cheaper to fly into Grand Cayman or Berkshires?

Prices for flights to both Berkshires and Grand Cayman change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Grand Cayman $39
    Berkshires $73

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Grand Cayman $41
    Berkshires $25

Tours and Activities in Grand Cayman

For Grand Cayman, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • West Bay Sightseeing Tour Plus Seven Mile Beach Visit: $45
  • Reagan’s Honey Beekeeping Adventure: $67
  • Stingraycity Adventure: $69
  • Starfish and Stingray City Fun Tour with Reef Snorkeling- 3 stops: $69
  • Stingray City Experience Plus One Snorkeling Stop: $69
  • Stingray City Sandbar, Coral Gardens and 7-Mile Beach Tour: $70
  • Stingray City Experience Plus Two Snorkeling Stops on Grand Cayman: $75
  • Stingrays, Starfish and Snorkeling Tour: $75
  • 2-stop Adventure: Stingray City and snorkeling at Cayman Reefs: $79
  • Grand Cayman Cruise: Starfish Point, Stingray City, Coral Garden: $80
  • Acquarius Stingray City and Snorkel Tours: $80
  • Cayman Adventure: Starfish Point, Stingray City and Coral Gardens: $99

Tours and Activities in Berkshires

Here are a few actual costs in Berkshires for available activities, ticket prices, and tours:

  • 2-Hour Guided Private Forest Bathing Experience Lenox: $40

Alcohol
  • Alcohol Drinks for one day
    Grand Cayman $13
    Berkshires $31
Typical Alcohol Prices in Grand Cayman

Below are a few samples from actual travelers for alcohol and nightlife costs in Grand Cayman:


  • Beer
    $4.97

Sample the Local Flavors in Grand Cayman

Here are a few nightlife and alcohol tours and activities from local tour providers in Grand Cayman:

  • Cayman Spirits Co. Distillery Tour Pass Ticket Only: $24


When comparing the travel costs between Grand Cayman and Berkshires, we can see that Berkshires is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Even though Grand Cayman is in Caribbean Islands and Berkshires is in North America, both of these destinations have relatively similar prices of travel. Generally, the levels of luxury and expenses are the same for these cities even though they are geographically far apart.

If you're trying to decide if either of these two destinations are within your price range, also see Is Grand Cayman Expensive? and Is Berkshires Expensive?.



When is the best time to visit Grand Cayman or Berkshires?

Berkshires has a temperate climate with four distinct seasons, but Grand Cayman experiences a warm climate with fairly sunny weather most of the year.

Should I visit Grand Cayman or Berkshires in the Summer?

Both Berkshires and Grand Cayman during the summer are popular places to visit. Plenty of visitors come to Grand Cayman because of the warm climate and sunshine that lasts throughout the year.

In July, Grand Cayman is generally a little warmer than Berkshires. Daily temperatures in Grand Cayman average around 28°C (83°F), and Berkshires fluctuates around 72°F (22°C).

It rains a lot this time of the year in Grand Cayman. Grand Cayman usually gets more rain in July than Berkshires. Grand Cayman gets 179 mm (7 in) of rain, while Berkshires receives 2.7 inches (69 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Grand Cayman 28°C (83°F) 
    Berkshires 72°F (22°C)

Should I visit Grand Cayman or Berkshires in the Autumn?

The autumn attracts plenty of travelers to both Grand Cayman and Berkshires. Warm weather and sunshine bring visitors to Grand Cayman year-round.

Grand Cayman is much warmer than Berkshires in the autumn. The daily temperature in Grand Cayman averages around 27°C (81°F) in October, and Berkshires fluctuates around 51°F (11°C).

Grand Cayman gets a good bit of rain this time of year. In October, Grand Cayman usually receives more rain than Berkshires. Grand Cayman gets 238 mm (9.4 in) of rain, while Berkshires receives 2.6 inches (67 mm) of rain each month for the autumn.


  • Autumn Average Temperatures October
    Grand Cayman 27°C (81°F) 
    Berkshires 51°F (11°C)

Should I visit Grand Cayman or Berkshires in the Winter?

The winter brings many poeple to Grand Cayman as well as Berkshires. Grand Cayman attracts visitors year-round for its warm weather and sunny climate.

Be prepared for some very cold days in Berkshires. In the winter, Grand Cayman is much warmer than Berkshires. Typically, the winter temperatures in Grand Cayman in January average around 24°C (76°F), and Berkshires averages at about 22°F (-6°C).

Grand Cayman usually gets more rain in January than Berkshires. Grand Cayman gets 58 mm (2.3 in) of rain, while Berkshires receives 1.9 inches (49 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Grand Cayman 24°C (76°F) 
    Berkshires 22°F (-6°C)

Should I visit Grand Cayman or Berkshires in the Spring?

Both Berkshires and Grand Cayman are popular destinations to visit in the spring with plenty of activities. The warm climate attracts visitors to Grand Cayman throughout the year.

In April, Grand Cayman is generally much warmer than Berkshires. Daily temperatures in Grand Cayman average around 26°C (79°F), and Berkshires fluctuates around 47°F (9°C).

In April, Grand Cayman usually receives less rain than Berkshires. Grand Cayman gets 48 mm (1.9 in) of rain, while Berkshires receives 2.6 inches (66 mm) of rain each month for the spring.


  • Spring Average Temperatures April
    Grand Cayman 26°C (79°F) 
    Berkshires 47°F (9°C)

Typical Weather for Berkshires and Grand Cayman

Grand Cayman Berkshires
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 24°C (76°F) 58 mm (2.3 in) 22°F (-6°C) 1.9 inches (49 mm)
Feb 24°C (76°F) 51 mm (2 in) 24°F (-4°C) 2 inches (51 mm)
Mar 25°C (77°F) 31 mm (1.2 in) 35°F (2°C) 2.5 inches (63 mm)
Apr 26°C (79°F) 48 mm (1.9 in) 47°F (9°C) 2.6 inches (66 mm)
May 27°C (81°F) 131 mm (5.1 in) 59°F (15°C) 3 inches (75 mm)
Jun 28°C (82°F) 183 mm (7.2 in) 67°F (20°C) 3.3 inches (83 mm)
Jul 28°C (83°F) 179 mm (7 in) 72°F (22°C) 2.7 inches (69 mm)
Aug 28°C (82°F) 172 mm (6.8 in) 70°F (21°C) 3 inches (76 mm)
Sep 28°C (82°F) 212 mm (8.3 in) 62°F (17°C) 2.8 inches (71 mm)
Oct 27°C (81°F) 238 mm (9.4 in) 51°F (11°C) 2.6 inches (67 mm)
Nov 26°C (79°F) 141 mm (5.6 in) 41°F (5°C) 2.9 inches (73 mm)
Dec 25°C (78°F) 57 mm (2.3 in) 28°F (-2°C) 2.7 inches (69 mm)